Preparation of n-acyl taurates



United States Patent 3,234,247 PREPARATHEN OF N-ACYL TAURATES Phillip G. Ahead, Chicago, Ill., and Andrew T. Guttman, Lakewood, Ohio, assignors to Armour and Company,

N-methyl-Z-pyrrolidone and 20 ml. of Xylene were added 1 g. of sodium methylate and 9.9 g. of sodium isethionate. The temperature was raised to 185 C. and held between 185 and 193 C. for two hours. The reaction mixture 5 was allowed to cool to room temperature and was then N aforpomhon of Delaware N 195 390 filtered. The filter cake was washed with methanol, then Drawing 2 n gfi ii With ethyl ether and dried by exposure to air. The product, a white powder, weighed 19.5 g. and contained 84% This invention relates to the preparation of surfactants, active as determined by titration with a Standard and more particularly to Igepon T-type detergents. Canon: so utlon' E We have discovered that by employing an inert solvent xample in a process in which a fatty amide is reacted with sodium To a solution at 155 C. of 14.3 g. of coco amide in isethionate in the presence of a basic catalyst, the yield a mixture consisting of 200 ml. of triethylene glycol dican be increased manyiold. F methyl ether and ml. of xylene was added 1 g. of A primary object of the invention, therefore, is to 10 sodium methylate. The temperature was raised to 160 provide a process for the preparation of a surfactant com- C. and 14.8 g. of sodium isethionate was added. The pound in which a fatty amide in an inert solvent is heated temperature was then raised to 190 C. and maintained to reaction temperature in the presence of a basic catalyst between 190 and 198 C. for two hours. The reaction for the recovery of the desired surfactant compound. A 9 mixture was allowed to cool to room temperature. 150 further object is to provide a new method for the preparaml. of ethyl ether was added and the mixture filtered. The tion of an Igepon T-type surfactant or synthetic detergent filter cake was slurried with a mixture consisting of ethyl by employing a novel combination of steps. Other speether and acetone, then filtered and dried by heating on a cific objects and advantages will appear as the specificasteam bath. The product weighed 27 g. and contained tion proceeds. 74% active material as determined by titration with a In one embodiment of our invention, we prepare a 20 standard cationic solution. surfactant compound by heating a fatty amide in an inert While, in the foregoing specification, we have set forth solvent with an excess of sodium isethionate and in the specific procedural steps in considerable detail for the presence of a basic catalyst to reaction temperatures and purpose of illustrating embodiments of the invention, it thereafter separate the resulting solid reaction product. will be understood that such detail or details may be By way of example, one mole of a fatty amide is con- 30 varied widely by those skilled in the art without departdensed in an inert solvent with an excess (10100% molar ing from the spirit of our invention. excess) of sodium isethionate in the presence of a basic We claim: compound as a catalyst and at a temperature of about 1. In a process for the preparation of a detergent com- 160 to 210 C. pound having the structure RCONI-ICH CH SO Na, The reaction may be described as follows: 30 wherein R is an alkyl chain having from 10 to 20 car- RC ONHz+HOCHzOH2SOaNa RCONHCHzGHzSOaNa-Hiz Alk. Catalyst Any basic catalyst may be employed, as, for example, bon atoms, the step of condensing a fatty amide in an an alkali metal, alkaline earth metal, hydroxide, alcoholinert solvent selected from the group consisting of polyate, hydride, amide, acetylide, etc. ethylene glycol ethers, N-methyl pyrrolidone and dimethyl The inert Solvent y be y flon-l'fiafltive Solvent. sulfoxide with an excess of sodium isethionate in the and examples f l be Oiled 3S P y yl glycol ethefs, presence of xylene and a basic compound as a catalyst, y pyfrolldone, dimethyl SulfOXld, and InlX- said basic compound being selected from the group contures 0f the solvents- D a sisting of alkali metals, alkaline earth metals, hydroxides, The temperatures are those at which reaction occurs, l h fl t hydrides, amides, and acetyhdes at a igg ,f gi g abltfimperatur? range of perature of from about 160 to 210 C. and 5 c. 6 pre era e range bemg between 180 2. The process of claim 1 in which the temperature Specific illustrative examples of the process may be 15 Within the Hinge of aboui 180T190 Set out as follows: e process of claim 1 wherein said sodium ise- Example I thionate has a molar excess of 10 to 100 percent. 1To a solution at 165 C. of 341 g. of hydrogenated References Cited by the Examiner ta low amide in a mixture consisting of 1200 ml. of tri- 5 ethylene glycol dimethyl ether, 800 ml. of diethylene 5 UNITED STATES PATENTS glycol dimethyl ether and 100 ml. of xylene were added 2,365,452 1/ 1945 Mack 260-401 18.5 g. of sodium methylate and 276 g. of sodium isethi- 2,432,850 94 Al ht 260-401 onate. The temperature was gradually raised to 188 C., by which time 350 ml. of solvent had distilled over. The OTHER REFERENCES reaction mixture was allowed to cool to room temperature, an equal volume of methanol added, and the resulting mixture filtered. The filter cake was washed with methanol, then with ether and dried by exposure to air. The product weighed 495 g., and contained active material as determined by titration with a standard cationic solution.

Example 11 To a solution at C. of 18.4 g. of hydrogenated tallow amide in a mixture consisting of 200 ml. of

Cited in Chemical Abstracts 51, 4357a (1957). McArdle, Use of Solvents in Synthetic Organic Chemistry, page 3, (1925), D. Van Nostrand Co., New York, NY.

Urushibara et a1., Bull. Inst. Chem. Res., Kyoto University 32, 159-167 (1954).

CHARLES B. PARKER, Primary Examiner. DANIEL D. HORWITZ, Examiner. 

1. IN A PROCESS FOR THE PREPARATION OF A DETERGENT COMPOUND HAAVING THE STRUCTURE RCONHCH2CH2SO3NA, WHEREIN R IS AN ALKYL CHAING HAVING FROM 10 TO 20 CARBON ATOMS, THE STEP OF CONDENSING A FATTY AMIDE IN AN INERT SOLVENT SELECTED FROM THE GROUP CONSISTING OF POLYETHYLENE GLYCOL ETHERS, N-METHYL PYRROLIDONE AND DIMETHYL SULFOXIDE WITH AN EXCESS OF SODIUM ISETHIONATE IN THE PRESENCE OF OXYLENE AND A BASIC COMPOUND AS A CATALYST, SAID BASIC COMPOUND BEING SELECTED FROM THE GROUP CONSISTING OF ALKALI METALS, ALKALINE EARTH METALS, HYDROXIDES, ALCOHOLATES, HYDRIDIES, AMIDES, AND ACETYLIDES AT A TEMPERATURE OF FROM ABOUT 160* TO 210*C. 